Series of Electronegativity Questions

Click For Summary
SUMMARY

This discussion centers on the concept of electronegativity and its implications in chemical bonding, particularly in Grignard reagents. It is established that an atom with high electronegativity, such as chlorine, can attract electrons from a less electronegative atom, like sodium, resulting in ionic charges. In the context of Grignard reagents (RMgX), the unique behavior of magnesium allows carbon to act as the electron-rich component, facilitating the formation of new carbon-carbon bonds when reacting with carbon dioxide (CO2). The interaction between electronegativities of carbon and oxygen in CO2 and the Grignard reagent is crucial for understanding the stability of the resulting compounds.

PREREQUISITES
  • Understanding of basic electronegativity concepts
  • Familiarity with Grignard reagents and their structure (RMgX)
  • Knowledge of ionic vs. covalent bonding
  • Basic principles of chemical reactions involving carbon compounds
NEXT STEPS
  • Study the properties and reactions of Grignard reagents in organic synthesis
  • Learn about the role of electronegativity in determining molecular polarity
  • Explore the concept of dipole moments in covalent bonds
  • Investigate the mechanisms of carbon-carbon bond formation in organic chemistry
USEFUL FOR

Chemistry students, organic chemists, and anyone preparing for examinations involving chemical bonding and reactions, particularly those focused on Grignard reagents and electronegativity concepts.

Superkevs22
Messages
14
Reaction score
0
Hi! I would like to know if what I'm thinking is correct. Please help me as to I'm confused :cry:

1. If atom "X" has a high Electronegativity, then that means that it can take Electrons from atom "Y" with a low Electronegativity easily causing atom "X" to have a more negative charge "-" and atom "Y" a more positive charge "+". Is this statement correct?

2. Considering statement number 1, does this mean that an atom with a high Electronegativity would most likely have a negative charge "-"?

3. How about a compound? For example is a Grignard reagent compound "RMgX" where "R" refers to any Hydrocarbon, "Mg" refers to Magnesium, and "X" as a halide. I would like to know how Electronegativity works with a Grignard reaction in forming a new carbon-carbon compound. When carbon dioxide "CO2" is added to the Grignard reagent. Here is what happens as shown in 3.1.

3.1. RMgX + CO2 -> RCOOMgX

Then you hydralize it to form the new carbon-carbon compound in 3.2.

3.2. RCOOMgX + H2O -> RCOOH + Mg(OH)X

Regarding that reaction, with the bonding of carbon in "R" and carbon "C", how was their Electronegativity affected (about the increase or decrease in Electronegativity or Charge so carbon "R" can form a bond with carbon "C") so they can form a bond as well as it's relationship with magnesium's "Mg" Electronegativity? I don't quite get the explanation in the link http://wiki.answers.com/Q/Why_Magnesium_is_necessary_for_Grignard's_reagent#slide1

If you could provide a simple and easy to understand explanation in layman's term if possible. I have an admission exam that will include this topic. Thank you. :frown:
 
Chemistry news on Phys.org
Superkevs22 said:
1. If atom "X" has a high Electronegativity, then that means that it can take Electrons from atom "Y" with a low Electronegativity easily causing atom "X" to have a more negative charge "-" and atom "Y" a more positive charge "+". Is this statement correct?
Yeah. Electronegativity just means how strongly an atom attracts electrons. Its more obvious with ionic compounds, when you react sodium metal with chlorine gas, you get sodium chloride. In that case that chlorine literally strips away sodiums single valence electron, so when you dissolve NaCl in water, you get a solution of Cl- anions, and Na+ cations. Sodium has an electronegativity of 0.93 and chlorine is 3.16 so that's a massive difference in electronegativity. Carbon on the other hand has an electronegativity of 2.55, so chlorine can't completely snatch its electrons like it does with sodium, but when chlorine bonds to carbon, chlorine still pulls carbons electron towards it, resulting in carbon being slightly more positively charged and chlorine slightly more negatively charged. The measure of the polarity of a bond is called a dipole moment. This diagram shows the dipole moments of some chlorinated methanes. The arrow points in the direction of the atom which hogs the electrons more.
15-6.gif




Superkevs22 said:
2. Considering statement number 1, does this mean that an atom with a high Electronegativity would most likely have a negative charge "-"?
Only if it steals an extra electron from somewhere. For example, if it reacts with a low electronegativity element like an alkali metal (i.e. lithium, sodium etc.) and forms an ionic bond. In chloromethane, the chlorine isn't actually negatively charged because its a covalent bond between it and carbon, meaning they share the electrons, chlorine doesn't fully take the electron from carbon. Rather than putting a - on the carbon, you use the delta symbol to indicate that it only partially takes the electrons:
320px-Polarity_%26_Umpolung.png


Superkevs22 said:
3. How about a compound? For example is a Grignard reagent compound "RMgX" where "R" refers to any Hydrocarbon, "Mg" refers to Magnesium, and "X" as a halide. I would like to know how Electronegativity works with a Grignard reaction in forming a new carbon-carbon compound. When carbon dioxide "CO2" is added to the Grignard reagent. Here is what happens as shown in
A Grignard reagent has unusual properties. Usually the halogen (X) would pull electrons away from carbon making the carbon more positively polarised, but in this case the magnesium atom gives the halogen an electron, so the halogen is no longer more electronegative than carbon. Now, carbon can be the one that snatches the electrons. So this is a rare case of carbon being the electron rich part of a molecule. Other examples of this are when carbon bonds to lithium. In a Grignard reagent, you can consider the carbon to be negatively charged.

Superkevs22 said:
3.1. RMgX + CO2 -> RCOOMgX

Then you hydralize it to form the new carbon-carbon compound in 3.2.

3.2. RCOOMgX + H2O -> RCOOH + Mg(OH)X

Regarding that reaction, with the bonding of carbon in "R" and carbon "C", how was their Electronegativity affected (about the increase or decrease in Electronegativity or Charge so carbon "R" can form a bond with carbon "C") so they can form a bond as well as it's relationship with magnesium's "Mg" Electronegativity? I don't quite get the explanation in the link http://wiki.answers.com/Q/Why_Magnesium_is_necessary_for_Grignard's_reagent#slide1

If you could provide a simple and easy to understand explanation in layman's term if possible. I have an admission exam that will include this topic. Thank you. :frown:

Oxygen is a very electronegative element so in carbon dioxide, the oxygen pulls electrons away from carbon, resulting in the carbon being more positively charged. In this case, the carbon needs more electrons. In the Grignard reagent, its the other way around, the carbon has more electrons than it needs, so the CO2 carbon is attracted to it, and grabs its electrons to form a new carbon-carbon bond. Basically what happens there is both the electronegative carbon (from the CO2) and the electropositive carbon (from the Grignard reagent) neutralise each other. Neutral compounds are more stable. Now they both have more similar electronegativities.
 
Last edited:
  • Like
Likes   Reactions: 1 person
Thank you so much for the response CrimpJiggler! I appreciate it a lot that you have not only provided the answers that I was looking for but you also took the time to illustrate it so it will be easier to understand. You saved me. Thanks a lot! =)
 

Similar threads

  • · Replies 6 ·
Replies
6
Views
4K
  • · Replies 3 ·
Replies
3
Views
4K
  • · Replies 2 ·
Replies
2
Views
4K
  • · Replies 4 ·
Replies
4
Views
2K
  • · Replies 5 ·
Replies
5
Views
4K
Replies
1
Views
3K
Replies
4
Views
4K
  • · Replies 3 ·
Replies
3
Views
3K
  • · Replies 19 ·
Replies
19
Views
9K
  • · Replies 1 ·
Replies
1
Views
5K